Prostaglandins of the F series

Abstract

The present invention provides new compounds, 13,14-dihydro-15-keto-PGFs, and vassopressors containing them, which raise blood pressure without substantial ephemeral depression of blood pressure, trachea or enteron contraction effect inherent in usual PGFs.

What is claimed is: 
     
       1. A 13,14-dihydro-15-keto-PGF represented by the formula: in which a bond between C-2 and C-3 is a single or a double bond, X is a group: ##STR37## R 1  is a hydrogen atom or a C 1-4  alkyl, phenyl, benzoyl, hydroxyalkyl, alkoxyalkyl, trialkylsilyl or tetrahydropyranyl group;   R 2  is a hydrogen atom or a lower alkyl group;   R 3  is hydroxyl;   R 3'   is hydroxyl; R 4  and R 5  are independently a hydrogen atom or a lower alkyl group, R 6  is a C 1-9  alkyl group containing a C 1-2  alkoxy substituent or ##STR38## (wherein R 7  is a hydrogen or halogen atom or a halogenated methyl group; and a physiologically acceptable salt of said 13,14-dihydro-15-keto-PGF.   
     
     
       2. The 13,14-dihydro-15-keto-PGF of claim 1, wherein R 1  is a C 1-4  alkyl group. 
     
     
       3. The 13,14-dihydro-15-keto-PGF according to claim 1, wherein at least one of R 4  and R 5  is a lower alkyl group, or a physiologically acceptable salt thereof. 
     
     
       4. The 13,14-dihydro-15-keto-PGF of claim 1 comprising a 13,14-dihydro-15-keto-16-substituted-PGF represented by the formula: ##STR39## or a physiologically acceptable salt thereof. 
     
     
       5. The 13,14-dihydro-15-keto-PGF according to claim 1, wherein each of R 4  and R 5  is a lower alkyl group, or a physiologically acceptable salt thereof. 
     
     
       6. The 13,14-dihydro-15-keto-PGF according to claim 1, comprising a 13,14-dihydro-15-keto-16-desbutyl-16-trifluoromethyl-phenoxy-PGF or a physiologically acceptable salt thereof. 
     
     
       7. A 13,14-dihydro-15-keto-PGF represented by the formula: ##STR40## in which a bond between C-2 and C-3 is a single or a double bond, X is a group: ##STR41## R 1  is a hydrogen atom or a C 1-4  alkyl, phenyl, benzoyl, hydroxyalkyl, alkoxyalkyl, trialkylsilyl or tetrahydropyranyl group; R 2  is a hydrogen atom or a lower alkyl group;   R 3  is hydroxyl;   R 3'  is hydroxyl; R 4  and R 5  are independently a hydrogen atom or a lower alkyl group, R 6  is a c 6-9  alkyl group which may be branched or contain a double bond; and a physiologically acceptable salt of said 13,14-dihydro-15-keto-PGF.   
     
     
       8. The 13,14-dihydro-15-keto-PGF of claim 7, wherein R 1  is a C 1-4  alkyl group. 
     
     
       9. The 13,14-dihydro-15-keto-PGF according to claim 7, wherein at least one of R 4  and R 5  is a lower alkyl group, or a physiologically acceptable salt thereof. 
     
     
       10. The 13,14-dihydro-15-keto-PGF according to claim 7, wherein each of R 4  and R 5  is a lower alkyl group, or a physiologically acceptable salt thereof. 
     
     
       11. A 13,14-dihydro-15-keto-20-ethyl-PGF represented by the formulae: ##STR42## in which a bond between C-2 and C-3 is a single or a double bond, X is a group: ##STR43## R 1  is a hydrogen atom or a C 1-4  alkyl, phenyl, benzoyl, hydroxyalkyl, alkoxyalkyl, trialkylsilyl or tetrahydropyranyl group; R 2  is a hydrogen atom or a lower alkyl group;   R 3  is hydroxyl;   R 3'  is a hydroxyl; R 4  and R 5  are independently a hydrogen atom or a lower alkyl group or a physiologically acceptable salt thereof.   
     
     
       12. A 13,14-dihydro-15-keto-PGF of claim 7 being a 13,14-dihydro-15-keto-20-ethyl-PGF 1 α, a C 1  -C 4  alkyl ester or a physiologically acceptable salt thereof. 
     
     
       13. A 13,14-dihydro-15-keto-PGF of claim 7 being a 13,14-dihydro-15-keto-20-ethyl-PGF 1 α isopropyl ester.